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Synthesis, Crystal Structure and Biological Activity of N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine

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Abstract

The title compound, N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine (C16H20N4O3S) was prepared from the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with N′-tert-Butyl-3-methoxylbenzohydrazine, and its structure was characterized by 1Hydrogen Nuclear Magnetic Resonance, High-Resolution Mass Spectrometry, IR spectra, and single crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P 21/c with cell parameters a = 17.986(2) Å, b = 8.0180(10) Å, c = 12.0190(14) Å, α = 90°, β = 91.160(5)°, γ = 90°, V = 1732.9(4) Å3, Z = 4, D c  = 1.335 g/cm3, μ (Mo Ka) = 0.209 mm−1, F (000) = 736, R = 0.0367 and wR = 0.0932. X-ray diffraction analysis indicates that all rings in the title compound are non-planar. The bioassay results indicated that, the title compound had good fungicide activity against Sclerotinia sclerotiorum, certain extent of insecticidal activity against Plutella xylostella L.

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Acknowledgments

This study was funded in part by grants from the National Natural Science Foundation of China (Nos. 20872071 and 20911120069), the Natural Science Foundation of Tianjin (10JCZDJC17500), the National Key Project for Basic Research (2010CB126105), National Key Technology Research and Development Program (2011BAE06B02 and 2011BAE06B05) and the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology (201002250); The Common Wealth Specialized Research Fund of China Agriculture (nyhyzx3-21, 201103016 and 201003029), and the Russian Foundation for Basic Research (Grant Numbers RFBR 08-03-00376a and RFBR/NNSF 08-03-92208 a).

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Authors and Affiliations

  1. Department of Plant Pathology, Sichuan Agricultural University, No. 555 Northeast Road, Wenjiang District, Chengdu, 611130, Sichuan, China

    Jie Huang & Yun Huang

  2. State Key Laboratory of Elemento Organic Chemistry, Nankai University, 94 Weijin Road, Nankai District, Tianjin, 300071, China

    Jie Huang, Huan Wang, Zhi-Jin Fan, Hai-Bin Song & Hui Zhao

  3. The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU, Ekaterinburg, Russia, 620002

    Polina E. Prokhorova, Nataliya P. Belskaya, Yury Yu. Morzherin & Vasiliy A. Bakulev

Authors
  1. Jie Huang
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  2. Huan Wang
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  3. Zhi-Jin Fan
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  4. Hai-Bin Song
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  5. Hui Zhao
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  6. Yun Huang
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  7. Polina E. Prokhorova
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  10. Vasiliy A. Bakulev
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Corresponding authors

Correspondence to Zhi-Jin Fan or Yun Huang.

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Jie Huang and Huan Wang contributed equally to this work.

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Huang, J., Wang, H., Fan, ZJ. et al. Synthesis, Crystal Structure and Biological Activity of N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine. J Chem Crystallogr 41, 1860–1865 (2011). https://doi.org/10.1007/s10870-011-0189-1

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  • DOI: https://doi.org/10.1007/s10870-011-0189-1

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